Airbnb Properties for Sale in Oakland, FL

Looking for a vacation rental investment in Oakland, FL with high ROI ?

Explore a range of newly added short-term rental homes in Oakland, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Oakland, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2127 BAY LINE ROAD Oakland, FL WELCOME HOME TO HULL ISLAND! This home offers a serene retreat for those looking for a ble...	4 beds \| 4 baths \| 2,858 sq.ft.	$650,000	Airbnb cash on cash: 4.34% Traditional cash on cash: 3.64% Airbnb Rental Income: $5064 Traditional Rental Income: $3607 Airbnb ROI: 4.34% Traditional ROI: 3.64%
1873 WHITE FEATHER LOOP Oakland, FL This well-designed 4-bedroom, 3-bathroom home with a private office is located in one of O...	4 beds \| 3 baths \| 2,418 sq.ft.	$579,000	Airbnb cash on cash: 4.96% Traditional cash on cash: 2.86% Airbnb Rental Income: $5064 Traditional Rental Income: $2899 Airbnb ROI: 4.96% Traditional ROI: 2.86%
1787 WHITE FEATHER LOOP Oakland, FL **This home qualifies for loan options with NO DOWN PAYMENT required, 100% financing avail...	3 beds \| 3 baths \| 2,152 sq.ft.	$525,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 3.25% Airbnb Rental Income: $3912 Traditional Rental Income: $2839 Airbnb ROI: 3.72% Traditional ROI: 3.25%
1877 STANDING ROCK CIRCLE Oakland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	3 beds \| 2 baths \| 2,008 sq.ft.	$520,000	Airbnb cash on cash: 3.71% Traditional cash on cash: 2.56% Airbnb Rental Income: $3912 Traditional Rental Income: $2515 Airbnb ROI: 3.71% Traditional ROI: 2.56%
1301 JOHNS COVE LANE Oakland, FL Back on the market! Huge price improvement!! Motivated sellers! Donât miss out on this ...	4 beds \| 2 baths \| 2,495 sq.ft.	$749,999	Airbnb cash on cash: 3.87% Traditional cash on cash: 2.46% Airbnb Rental Income: $5064 Traditional Rental Income: $3046 Airbnb ROI: 3.87% Traditional ROI: 2.46%
500 W OAKLAND AVENUE Oakland, FL One or more photo(s) has been virtually staged. Charming Renovated Home in the Heart of Hi...	3 beds \| 2 baths \| 1,336 sq.ft.	$375,000	Airbnb cash on cash: 6.41% Traditional cash on cash: 4.58% Airbnb Rental Income: $3912 Traditional Rental Income: $2425 Airbnb ROI: 6.41% Traditional ROI: 4.58%
409 E GULLEY AVENUE Oakland, FL Tucked away in the heart of downtown Oakland, this adorable 3-bedroom, 2-bathroom home cap...	3 beds \| 2 baths \| 1,630 sq.ft.	$500,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 3.38% Airbnb Rental Income: $3912 Traditional Rental Income: $2530 Airbnb ROI: 4.54% Traditional ROI: 3.38%
1382 FOLTZ LOOP Oakland, FL Under contract-accepting backup offers. **ASSUMABLE VA MORTGAGE AT A 5.375 INTEREST RATE...	4 beds \| 3 baths \| 2,268 sq.ft.	$648,900	Airbnb cash on cash: 4% Traditional cash on cash: 2.09% Airbnb Rental Income: $5064 Traditional Rental Income: $2876 Airbnb ROI: 4% Traditional ROI: 2.09%
310 E GULLEY AVENUE Oakland, FL Under contract-accepting backup offers. Welcome to 310 E Gulley Aveâthis inviting 3-bedr...	3 beds \| 2 baths \| 1,419 sq.ft.	$489,000	Airbnb cash on cash: 5.21% Traditional cash on cash: 3.92% Airbnb Rental Income: $3912 Traditional Rental Income: $2482 Airbnb ROI: 5.21% Traditional ROI: 3.92%
610 STRIHAL LOOP Oakland, FL * Seller is giving $10,000 in concessions for closing costs/prepaids or a rate buy down. W...	4 beds \| 2 baths \| 2,490 sq.ft.	$585,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 2.98% Airbnb Rental Income: $5064 Traditional Rental Income: $2640 Airbnb ROI: 5.52% Traditional ROI: 2.98%
312 W HULL AVENUE Oakland, FL Discover the wonderful blend of functionality, efficiency, and flexibility in this beautif...	4 beds \| 2 baths \| 1,681 sq.ft.	$495,000	Airbnb cash on cash: 6.58% Traditional cash on cash: 3.02% Airbnb Rental Income: $5064 Traditional Rental Income: $2384 Airbnb ROI: 6.58% Traditional ROI: 3.02%
2035 WHITE FEATHER LOOP Oakland, FL Welcome to 2035 White Feather Loop, a stunning haven nestled in the serene community of Oa...	3 beds \| 3 baths \| 2,082 sq.ft.	$550,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 3.14% Airbnb Rental Income: $3912 Traditional Rental Income: $2766 Airbnb ROI: 3.74% Traditional ROI: 3.14%
233 LARGOVISTA DRIVE Oakland, FL Luxury, Convenience, and Comfort in Johnâs Landing! This thoughtfully updated and move-i...	4 beds \| 2 baths \| 2,176 sq.ft.	$534,900	Airbnb cash on cash: 5.94% Traditional cash on cash: 2.74% Airbnb Rental Income: $5064 Traditional Rental Income: $2431 Airbnb ROI: 5.94% Traditional ROI: 2.74%
2755 BOBCAT CHASE BOULEVARD Oakland, FL Live just minutes from the charm of Downtown Winter Garden in the desirable Oakland commun...	3 beds \| 3 baths \| 1,822 sq.ft.	$514,913	Airbnb cash on cash: 3.61% Traditional cash on cash: 2.59% Airbnb Rental Income: $3912 Traditional Rental Income: $2583 Airbnb ROI: 3.61% Traditional ROI: 2.59%
2435 STANDING ROCK CIRCLE Oakland, FL Perfectly situated in the desirable Oakland Trails neighborhood this perfectly updated and...	4 beds \| 3 baths \| 2,017 sq.ft.	$528,000	Airbnb cash on cash: 5.52% Traditional cash on cash: 2.79% Airbnb Rental Income: $5064 Traditional Rental Income: $2685 Airbnb ROI: 5.52% Traditional ROI: 2.79%
2163 WHITE FEATHER LOOP Oakland, FL *Seller is offering $10,000 closing cost contribution to any buyer!*This recently buil...	3 beds \| 3 baths \| 1,744 sq.ft.	$489,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 2.91% Airbnb Rental Income: $3912 Traditional Rental Income: $2441 Airbnb ROI: 4.28% Traditional ROI: 2.91%
2120 GOPHER TORTOISE TERRACE Oakland, FL ***Rare Financial Advantage- Low interest rate of 2.75% ASSUMABLE LOAN is available with a...	3 beds \| 3 baths \| 1,620 sq.ft.	$393,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 2.99% Airbnb Rental Income: $3912 Traditional Rental Income: $2385 Airbnb ROI: 4.85% Traditional ROI: 2.99%
309 W OAKLAND AVENUE Oakland, FL Seller is willing to give concessions towards closing costs! Charming Renovated Home in ...	4 beds \| 3 baths \| 2,386 sq.ft.	$779,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 2.38% Airbnb Rental Income: $5064 Traditional Rental Income: $3058 Airbnb ROI: 3.72% Traditional ROI: 2.38%
2023 WHITE FEATHER LOOP Oakland, FL One or more photo(s) has been virtually staged. Your dream home is waiting for you! This h...	3 beds \| 3 baths \| 2,089 sq.ft.	$475,000	Airbnb cash on cash: 3.92% Traditional cash on cash: 3.23% Airbnb Rental Income: $3912 Traditional Rental Income: $2766 Airbnb ROI: 3.92% Traditional ROI: 3.23%
2090 STANDING ROCK CIRCLE Oakland, FL Stunning Home in Oakland Trails! This immaculate 3-bedroom, 2.5 bath home blends thoughtf...	3 beds \| 3 baths \| 2,000 sq.ft.	$649,900	Airbnb cash on cash: 3.14% Traditional cash on cash: 2.66% Airbnb Rental Income: $3912 Traditional Rental Income: $2777 Airbnb ROI: 3.14% Traditional ROI: 2.66%
1143 BOBCAT CHASE BOULEVARD Oakland, FL One or more photo(s) has been virtually staged. Take advantage of a 1% of the loan amount ...	3 beds \| 3 baths \| 1,811 sq.ft.	$510,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 2.27% Airbnb Rental Income: $3912 Traditional Rental Income: $2608 Airbnb ROI: 3.24% Traditional ROI: 2.27%
326 LARGOVISTA DRIVE Oakland, FL Welcome to your dream home in the highly sought-after Johns Landing community! This immacu...	4 beds \| 3 baths \| 3,182 sq.ft.	$699,900	Airbnb cash on cash: 3.69% Traditional cash on cash: 2.92% Airbnb Rental Income: $5064 Traditional Rental Income: $3527 Airbnb ROI: 3.69% Traditional ROI: 2.92%

Vacation Rentals in Oakland

There are 22 vacation rental properties available for sale in the city of Oakland . The median list price of Airbnb properties available for sale in Oakland is $564,500 and the average price per square foot is $235. The cash on cash return on vacation rentals in Oakland is 4.00%. The average monthly short term rental income in Oakland is $3,912.

Oakland, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 22 Airbnb properties available for sale in Oakland.

In 2025, the best neighborhood to buy short term rental property is Oakland.

In September 2025, the average Airbnb occupancy rate in Oakland is 72%.

Airbnb data on vacation rentals in Oakland, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Oakland, FL market insights, guest information and booking details, seasonality trends and historical Oakland, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Oakland, FL

2127 BAY LINE ROAD

Oakland, FL

4 beds | 4 baths | 2,858 sq.ft.

$650,000

Airbnb cash on cash: 4.34%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $5064

Traditional Rental Income: $3607

Airbnb ROI: 4.34%

Traditional ROI: 3.64%

1873 WHITE FEATHER LOOP

Oakland, FL

4 beds | 3 baths | 2,418 sq.ft.

$579,000

Airbnb cash on cash: 4.96%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $5064

Traditional Rental Income: $2899

Airbnb ROI: 4.96%

Traditional ROI: 2.86%

1787 WHITE FEATHER LOOP

Oakland, FL

3 beds | 3 baths | 2,152 sq.ft.

$525,000

Airbnb cash on cash: 3.72%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $3912

Traditional Rental Income: $2839

Airbnb ROI: 3.72%

Traditional ROI: 3.25%

1877 STANDING ROCK CIRCLE

Oakland, FL

3 beds | 2 baths | 2,008 sq.ft.

$520,000

Airbnb cash on cash: 3.71%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $3912

Traditional Rental Income: $2515

Airbnb ROI: 3.71%

Traditional ROI: 2.56%

1301 JOHNS COVE LANE

Oakland, FL

4 beds | 2 baths | 2,495 sq.ft.

$749,999

Airbnb cash on cash: 3.87%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $5064

Traditional Rental Income: $3046

Airbnb ROI: 3.87%

Traditional ROI: 2.46%

500 W OAKLAND AVENUE

Oakland, FL

3 beds | 2 baths | 1,336 sq.ft.

$375,000

Airbnb cash on cash: 6.41%

Traditional cash on cash: 4.58%

Airbnb Rental Income: $3912

Traditional Rental Income: $2425

Airbnb ROI: 6.41%

Traditional ROI: 4.58%

409 E GULLEY AVENUE

Oakland, FL

3 beds | 2 baths | 1,630 sq.ft.

$500,000

Airbnb cash on cash: 4.54%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $3912

Traditional Rental Income: $2530

Airbnb ROI: 4.54%

Traditional ROI: 3.38%

1382 FOLTZ LOOP

Oakland, FL

4 beds | 3 baths | 2,268 sq.ft.

$648,900

Airbnb cash on cash: 4%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $5064

Traditional Rental Income: $2876

Airbnb ROI: 4%